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An UrbanDaddy Publication

Our comrades in style over at UrbanDaddy Perks recently teamed up with Maine’s most sought-after cobblers, Rancourt & Co., to offer a few exclusive styles of their boat shoe and ranger mocs—each of which comes in a chili pebble-grain upper or a suede that looks a lot like our favorite malbec. And we had the opportunity to catch up with Kyle Rancourt, third-generation cobbler and all-round stand-up guy, to talk footwear.

The good news is, this one features a lot more Sofia Vergara from Esquire and a 100 points of spring style from GQ, among other things. Naturally, we don’t agree with every last piece of it, so we’ve provided a running commentary for this month’s print crop, separating the sublime from the ridiculous. Consider this the Cliffs Notes version.

Now that we’re fully into sockless season, we’re noticing a lot of multicolored boat shoes around. It’s only natural for the boat shoe to get a bit peacocky now that it’s been in the trend spotlight for a few seasons…but we didn’t expect the result to be quite so sharp.

The beginner versions are from standbys like Sebago and Sperry (the latter is reportedly Errol Morris’ favorite shoe), but those are just your subdued options. Once you’ve graduated to the genuinely eye-popping models, you can entertain yourself with Yuketen and Band of Outsiders’ latest. Imagine that flood of colors next to a blanched khaki and a bare ankle…and you’ll start to see why we’re so excited.

And judging by the neon-hued Sperrys at Band of Outsiders’ Pitti show, this is just the beginning.

This Tretorn item won’t be in stores until March, but we couldn’t resist a quick preview. As you can tell from the cord around the heel, it’s very much a boat shoe, but the laces in front have been swapped out for a monkstrap-style band—combining two of our favorite kinds of shoe. It’s a good idea, and not just because of the casual loafer vibe. By our lights, the top-sider is ripe for a few forward-thinking twists, and this is the best one we’ve seen so far.

The boat shoe has seen a lot of permutations over the past year, but this might be our favorite. It’s from Band of Outsiders’ ongoing Sperry collab, and it’s entirely painted on. That’s right, you’re looking at the world’s first trompe l'oeil topsider.

The shoe itself is a low-top rubber galosh—a more convenient version of what you’d be wearing if you were actually working on a boat—but the print turns it into a cheeky take on the recent glut of nautical footwear. Just don’t wear it with socks.

By now, we imagine you’re pretty familiar with the casual charm of boat shoes, but here’s a twist you may not have anticipated: the boat pant.

If these Opening Ceremony grommet pants look familiar, it’s probably because you’ve seen that same threaded-cord look on dozens of pairs of Sperrys by now. This is just the first time it’s moved up to the waistline.

Use it right and it could add a deckhand vibe to just about any summer outfit you’ve got—but for moderation’s sake, you’ll want to avoid wearing them both at once.

Now that it’s warm enough to make every square inch of exposed skin count, we thought we’d offer a few helpful tips on going sockless. As you can see above, it’s a pretty great look when executed properly—somewhere between an Italian painter and an unusually stylish surf bum—but the key to this particular move is finding the right shoe. That means boat shoes, moccasins, loafers, bucks, bluchers and anything canvas. By the same token, we’d stay away from sneakers, wing-tips and anything more formal. And remember: life’s too short to worry about a little sweat.